A Weekend in the Windy City: Eats, Views & Vibes

From sky-high views and legendary landmarks to lush parks, modern art, and local comedy, Chicago is packed with iconic experiences!

Skyline views & iconic photo ops

• The Bean (Cloud Gate): It’s touristy, but a must-see! Best early morning or golden hour for photos.

• 360 CHICAGO (John Hancock Observatory): Get sweeping lakefront and skyline views with shorter lines than Willis. Brave the TILT platform for a literal lean out over the city. Great place to watch the sunset!

• Willis Tower Skydeck (The Ledge): Step onto a glass box 1,353 feet above the city for the ultimate tourist photo. You must buy a ticket ahead!

Parks, fountains & outdoor vibes

• Chicago Riverwalk: Walkable, scenic, and full of energy. Grab a drink, rent a kayak, or just enjoy the city from the water level.

• Millennium Park: Beyond The Bean, enjoy public art, lush gardens, splash fountains, and sometimes live music at the Jay Pritzker Pavilion.

• Buckingham Fountain (Grant Park): A sunset stunner. Nighttime lights and music shows make it feel extra cinematic. It's a close walk from The Bean.

• Navy Pier: Yes, it’s touristy, but it offers fireworks in summer, boat rides, and the Centennial Wheel with lake views.

• Lincoln Park Zoo & Conservatory: Go to check out the animals, greenery, and Victorian glasshouses. It's a great little adventure and it's free!

Culture, museums & architecture

• Architecture boat tour: This is a must-do! It's the top tour in Chicago for a reason. Gorgeous skyline views and deep insight into the city’s design legacy.

• Museum of Contemporary Art (MCA Chicago): Compact but bold with great edgy exhibits!

Entertainment & local flavor

• Second City (Old Town): This legendary comedy club launched the likes of Tina Fey and Steve Carell. Shows going on every night, but I recommend booking in advance, especially on weekends!

• Wrigley Field (Wrigleyville): Catch a Cubs game or tour the historic stadium. Even if you’re not into baseball, the neighborhood buzz on game days is worth experiencing!

For foodies & night owls

• West Loop: Chic and industrial. Home to the Time Out Market and endless food and cocktail spots. A great area to go for dinner and drinks.

• Logan Square: Cool and casual with dive bars, vintage shops, and awesome eating spots. Great to go in the daytime for chill vibes or a low-key night out.

• Wicker Park / Bucktown: Artsy, indie, and very walkable. Lots of thrift shops, record stores, coffee shops, and murals. Definitely check out the 606 Trail!

For architecture, shopping & sights

• Michigan Avenue (The Magnificent Mile): Luxury shops meet architectural icons. Home to Tribune Tower, historic hotels, and flagship stores. To avoid the crowds, go early!

• Old Town: Cobblestone charm, Victorian homes, and Second City comedy. A lovely area for afternoon exploring.

Whether you're needing to try deep-dish, check out a rooftop, or splurge on a high-end restaurant, Chicago delivers.

Classic Chicago eats (iconic & local favorites)

• Gino’s East (near North Side): Amazing gooey, cheesy pizza and a crunchy, cornmeal-crusted deep dish. The place has graffiti-covered walls adding to the atmosphere!

• Lou Malnati’s (various locations): Locals love the deep dish here for a reason—its butter crust is unmatched. Go classic with sausage deep-dish and a side of Malnati salad.

• Pequod’s Pizza (Lincoln Park): A cult favorite for its caramelized cheese crust. Less touristy, more authentic Chicago vibe.

  • Tip: Call ahead—since they don’t take reservations, the wait time can get crazy!

• Portillo’s & Barnelli’s (River North): A must stop for Chicago dogs, Italian beef, and the famous chocolate cake shake. All amazing!

• The Wiener’s Circle (Lincoln Park): Iconic for char dogs and even more so for the late-night banter from staff (it’s part of the experience). Late-night only!

• Flub A Dub Chub’s (Lakeview East): Retro diner with personality. Known for juicy burgers, hot dogs, and good vibes. No ketchup!

Fine dining (for a splurge)

• Alinea (Lincoln Park): A three-Michelin-star restaurant, this is avant-garde, immersive dining at its most theatrical. The helium sugar balloon is legendary. You must book months in advance!

• Oriole (West Loop): A two-Michelin-star restaurant, it is a quieter, more intimate experience. Each course is thoughtful and surprising. I highly recommend the tasting menu.

• Esmé (Lincoln Park): Fine dining meets art exhibit experience. This one-Michelin-star restaurant has great seasonal, story-driven plates.

Trendy & upscale (stylish but more accessible)

• Girl & The Goat (West Loop): Bold flavors, inventive small plates. Don’t miss the roasted pig face or goat empanadas.

• Aba (Fulton Market): Mediterranean rooftop with great ambiance. Try the green falafel, whipped feta, and the pomegranate frozen cocktail. It is a great place to dine at sunset or for a weekend brunch.

• Avec (West Loop): Cozy, communal dining with Mediterranean flair. I recommend the chorizo-stuffed dates and slow-roasted pork shoulder.

• Arts Club Café at RH Chicago (Gold Coast): A chic brunch under chandeliers in a luxury furniture showroom. You must try the avocado toast, truffle fries, and a latte. Great spot to relax and recharge!

Casual gems & local favorites

• Smoque BBQ (Irving Park): Low-key but famous for a reason. Ribs, brisket, and burnt ends are amazing and you should not miss them.

• Time Out Market (Fulton Market): Perfect for groups or indecisive eaters. Sample dishes from top local chefs all in one place. Be sure to also grab a drink at the upstairs bar for a great view of the skyline.

Whether you're in the mood for jazz-era nostalgia, rooftop glam, or tucked-away speakeasies, Chicago has it all! To act like a local, ask for a Chicago handshake!

Live music & vintage vibes

• Zebra Lounge (Gold Coast): Tiny, quirky piano bar where locals belt out show tunes and '80s hits with live accompaniment. I recommend going on the later side as it gets lively after 10 pm.

• Green Mill Cocktail Lounge (Uptown): Step into a 1920s time capsule where Al Capone once held court. Nightly live jazz, candlelit tables, and a no-frills bar. This is cash only!

Craft cocktails & speakeasy style

• The Violet Hour (Wicker Park): Moody, velvet-draped cocktail lounge with no signage—look for the mural. Drinks are complex and artistic. Perfect for a night out when you want to dress up! Ask your server for a seasonal favorite.

• The Berkshire Room (River North): Inside the ACME Hotel, this dimly lit bar mixes sophistication with creativity. Great for pre-dinner drinks or nightcap dates.

Tropical escapes & tiki fun

• Three Dots and a Dash (River North): A hidden tiki bar down a back alley. Think glowing skull mugs, flaming garnishes, and Instagram-worthy presentation.

Laid-back & local

• Delilah’s (Lincoln Park): Dive bar meets whiskey haven. Punk rock on the speakers, a pool table in the back, and over 800 whiskeys on the shelf. You must ask for their daily bourbon pick or try a whiskey and beer combo.